


Broken but Better

by xKookiesandCreamx



Series: The Adventures of a Jock, a Nerd, and a Broken Nose [2]
Category: Teen Wolf (TV)
Genre: Alternate Universe - High School, Alternate Universe - No Hale Fire, Alternate Universe- No Supernatural, Anal Sex, Blowjobs, Embarassed Stiles, Everyone Is Alive, First Date, First Kiss, First Time, Frottage, Insecure Derek, Insecure Stiles Stilinski, Jock Derek, M/M, Nerd Stiles, Oral, Rimming, embarassed Derek
Language: English
Status: Completed
Published: 2016-07-19
Updated: 2016-07-19
Packaged: 2018-07-25 08:22:43
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,126
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7525375
Author URL: https://archiveofourown.org/users/xKookiesandCreamx/pseuds/xKookiesandCreamx
Summary: <blockquote class="userstuff">
              <p>After Stiles gets his wits about him, he and Derek finally get to have their first date, which leads to a lot of other...firsts.</p>
            </blockquote>





	Broken but Better

**Author's Note:**

> Holy hotcakes is this long! Anyways at the endnote of my other fic, Broken Nose, I asked if anyone would want a bonus first date scene or smut scene, and the general consensus was yes, so apparently my brain took that, ran with it, and spewed out that with a whole lotta extra. 
> 
> Also, for anyone who didn't read Broken Nose, hey there, what's good? Uh you don't technically have to read the last fic to get this one, but it may make this story a bit more sense. But *shrugs* you do you fam, you do you.

* * *

Stiles groggily woke up, and the first thing he took note of was the slightly hard, warm surface his head was resting on.

Looking up, Stiles discovered that the surface was none other than Derek Hale's abdomen, and then all the events of the day came roaring back to him in startling technicolor.

"Oh god" Stiles whispered, or at least thought he whispered, but judging by the jock stirring and then blinking open those kaleidoscope eyes, Stiles didn't succeed in his attempts at being quiet.

 

"Oh hey, you're awake! Do you...remember everything yet?" Derek tentatively asked.

Nodding, Stiles could feel his cheeks warm with what he could guess to be a startlingly red blush, and said "Yep. All of it."

Stiles however, was not prepared for the sunshine-rivaling smile that bloomed across Derek's face at his words.

"Oh, well...good" Derek said, grin still in place.

Stiles tried to mirror his expression, until, "Okay yeah ow forgot about what got us here" Stiles said, tentatively touching his white brace and bandaged covered nose.

"Yeah...i'm really sorry Stiles" Derek said, expression taking on that of guilt.

"Hey, it's okay, I mean it sucks, but it also got us here, so I can't complain."

 

"Well yeah that's true. Speaking of that...do you remember what you said while you were looped up on anesthesia? Your dad told me it would make you forget things but never told me whether you'd remember what you did after the effects wore off."

Stiles tried to think back to post-surgery him, and then remembered. Oh boy.

 

"Oh hmm...yeah? I uh...it's okay if you only agreed to the boyfriend thing because I was all loopy, I won't hold it against you."

"Hey no, Stiles I didn't agree because you were loopy...did you only say that because you were loopy?" Derek said, hesitancy marring his tone.

"Nope, I one hundred percent meant it, dude." 

"Oh. Well...good. And don't call me dude."

"Oh whatever...honey bunch" Stiles said, slight, shit eating smile adorning his face. 

"Nope. No way."

"Baby cakes?"

"No."

"Snugglekins?"

"No Stiles, just no." Derek said laughing.

"Hmm...fine. How about...Der?"

"That...that one might be fine."

"Oh yeah!" Stiles exclaimed, "Now, what about me?"

"You? Uh..." Derek said wracking his brain. "What about...Sti?"

"Sti? I mean...hmm yeah. Der and Sti...that works for me."

"Yeah?" Derek said, small smile on his lips.

"Yeah." Stiles said, returning the gesture.

 

It took a few seconds for Stiles to notice how close his and Derek's faces got.

"You know, Der...yeah I definitely like that...um, we never kissed remember? Your mom walked in right when we were about to."

"Oh yeah, huh, well...guess we"ll just have to fix that."

Stiles smiled, and the pair leaned it, until Derek stopped a couple inches away.

"Uh...Sti?"

"Yeah?"

"How are we-how are we gonna do this?" Derek asked, gesturing to the bandages on Stiles's nose.

"Oh right, yeah. How about we...just yeah like that" Stiles mumbled, until their faces turned enough to avoid impact of noses.

Then, Derek closed the distance, and Stiles, well Stiles swore he felt the planets align. The kiss was that good.

Breaking away a few moments later, Stiles sighed and said "Wow, if that's what it feels like when I feel like crap I can't even imagine what it'll feel like once my nose is healed."

"Oh yeah, tell me about it." Derek sighed.

* * *

 

It's been a week and a half since Stiles's surgery and Derek is excited.

Excited because today Stiles is going back to the hospital to see Derek's mom and have the cast removed and his nose looked at to make sure it healed properly.

Which means, they can finally,  _finally_ , really kiss. 

The past week and a half has been a blur of tentative, slightly chaste kisses, and Netflix marathons, because no matter how much Derek tried to convince Stiles that he looked good even with the splint, Stiles hasn't wanted to go out in public.

So, they haven't really had a proper date yet.

Stiles likes to call their Netflix, pizza, video games, and cuddle sessions dates, and Derek's not opposed to calling them as such, he just...wants a proper, real date.

(And maybe to make out with Stiles a little, and do other...things. I mean they've had sexual tension for forever and Derek finally wants to remedy it).

Derek may also want a slight break from the Sheriff coming home during Stiles's and Derek's hangouts, there's only so much cop glare he can take.

Stiles claims that the Sheriff likes him, is surprised at how nice of a boy he is, and holds Talia and all the Hales to the highest of regards...but he still has a gun, and well Derek, Derek doesn't want to experience the pain of a gunshot wound ever, especially not any time soon.

So, Derek is excited, and as he watches Stiles stumble slightly down his front steps and head to the Camaro, he grins.

* * *

 

"Alrighty, hello boys, good to see you" Talia says, walking into the room and putting gloves on.

Talia smiled at the simultaneous "Hey Mom" and "Hey Mrs. Hale" that followed.

"Now Stiles, I told you that you could call me Talia" She said as she approached the boy on the examination table.

"Oh right, sorry Mrs- I mean Talia" 

Smiling Talia slowly took off Stiles splint, and gently felt the bones.

"Everything seems to have healed perfectly Stiles, so you're good to go" Talia said, removing her gloves.

"Have a nice day boys, and...be safe!" Talia threw over her shoulder, laughing at the sputtering indignation and red faces of the boys.

 

Trying to shake off the embarrassment at Talia's statement, Stiles turns towards Derek, wiggling his nose and saying "So, how does it look?"

Derek, trying to fight off the last of his blush that his mother caused, look towards Stiles, taking in his nose's appearance, and noting how it looked just the same as before.

"Still cute" Derek said

"Oh okay good. Cute huh? Like...what was that that you said the last time we were here? Wasn't it something along the lines of...cute button nose?" Stiles said smirking.

"Sti..." Derek grumbled, rolling his eyes and blushing.

Stiles laughed, and hopped off the examination table, heading towards his boyfriend. Cradling his stubbly face, he leaned down and gave him his first splint-free kiss. 

Smiling, he asked "So, where you taking me?"

"I'm taking you home" Derek said, standing.

"Woah what? Der, I was just teasing, I'm sorry!"

At the look of panic crossing his boyfriend's face, Derek dropped his smirk, gently cradling Stiles's face.

"Hey no, Sti that's not what I meant. Well I mean...yeah but not like that. I mean i'm taking you home so you can get dressed up and then i'm going to pick your cute butt up at 7:30 for our first official date."

"Oh...oh okay yeah that's better. Why can't we just start now though? Why do I have to go home and then have you pick me up?" Stiles asked, following Derek out of the hospital and to the Camaro.

 

Derek could feel himself blush slightly as he opened the door and slid behind the wheel. 

"Because...I want to do it properly you know?"

"Oh, ohh I get you" Stiles said, slight smirk on his face letting Derek know that the next sentence out of his cupid's bow mouth was going to be teasing.

"So, Der does that mean you're gonna show up with flowers? Maybe give me your jacket to wear when it gets cold?"

"Shut up, Sti" Derek grumbled good naturedly, starting the car and heading towards the Stilinski's.

"You know i'm just teasing, Der" Stiles said, leaning over and giving the hazel eyed boy a kiss on the cheek when they pulled into his driveway.

"Yeah yeah" Derek said, rolling his eyes, pulling the amber eyed boy in for a definitely more than chaste kiss.

Pulling away, Derek smirked and said "Bye Sti", laughing lightly at the boy dazedly walking up to his front door and going inside.

* * *

 

Stiles stumbled down his stairs at the sound of his doorbell ringing.

Opening the door, Stiles didn't know whether to drool, laugh, or even cry at the sight before him.

That sight being Derek looking downright delectable in dark brown corduroy pants, and a forest green button down, with  _oh god with the sleeves rolled up to the elbows._

Stiles suddenly felt a little self conscious over his own dark tan corduroys and light blue button up.

But then, to top it all off, Derek was also holding a bouquet of yellow daffodils in his hand, and what looked to be his letterman jacket in his other.

 

"Oh god when I said the flowers and jacket thing I was just teasing Der you didn't have to actually do it!" Stiles exclaimed, taking note of the way Derek's face fell slightly, and was about to backtrack when Derek cut him off.

"Well I mean yeah I knew you were teasing but I also thought it was a cute idea...? I can just put everything in the backseat, yeah let me just do that" Derek said as he made to go back to the Camaro.

"Woah woah don't you dare move Derek Hale" Stiles said, grabbing Derek's elbow.

"You know my brain to mouth filter is very limited Der, and what I usually say doesn't come out the way I intended it to. When I said you didn't have to actually do it I didn't mean I was mad or embarrassed that you did, the complete opposite really. I meant you didn't have to go through all the trouble of doing it."

"It wasn't trouble doing this Sti, trust me. And even if it was, I would still do it, because it's for you." 

"Oh god you big lovable sap let's leave because the sooner we can go on this little date of yours the sooner I can get my hands on the ass in those couderoys and then properly make out with you like i've wanted to do for like two weeks now."

Chuckling at his boyfriend's antics, Derek waited for Stiles to close and lock his front door, and then opened the passenger side door for him.

"Oh god, i'm swooning right now, you're killing me Der." Stiles sighed.

Good, Derek smirked, heading for the driver's side of the Camaro.

* * *

 

When they entered the diner, Stiles couldn't help but smile, and that smile grew even more when Derek held the door open for him.

The pair followed the hostess to a booth, and sat down, perusing the menus, nodding when the hostess said their waitress, Brittany, would be right with them.

 

"So, I hope this is okay. I know you love curly fries, and this place is supposed to have the best ones in the area."

"Are you kidding me Der? This is awesome! I used to come here all the time with my mom, and now i'll come here mostly with Scott or sometimes my dad, and now you. So...more good memories to add to the place" Stiles said smiling.

Derek returned the expression, and looked at the menu.

 

The dinner passed by pleasantly and full of laughs and good food. The pair even shared a milkshake, strawberry, which they were both delighted to find they shared as a favorite, and Derek could not be happier with how the night's going, until they were given the check.

The check that was handed over by their waitress, Brittany, and included a phone number signed with her name and a heart at the end.

 

Now, Derek would be lying if he said he hadn't felt her eyes on him all night, and didn't take note of her blatant flirting attempts, but he paid little mind to it, as he was too busy taking in everything that is the greatness of Stiles Stilinski, and couldn't care less about the waitress.

He was planning on just ignoring her for the rest of the night, but now that was out of the realm of possibility, due to her shoving the check in his face and asking in a flirty tone "So..?"

 

"So...I have a boyfriend, like, right there. Have been on a date with him all night actually." Derek said gesturing to Stiles.

"You? With that? Oh please you could do so much better! You're like a 100 on the hotness scale and that thing is like a solid 3" The waitress sneered.

Derek was preparing to tell the bitch off, but was interrupted by a small sounding "Just drop it Der" from a very hurt looking Stiles.

 

Seeing such an expression on his boyfriend's face and such a tone escaping his lips, Derek got even more angry, and practically shouted "No, I will not drop it Stiles! Not when this poor excuse of a waitress wants to insult my beautiful boyfriend!" 

"Beautiful, right..." Stiles said sadly, grabbing his wallet and throwing down a couple 20s, and heading outside.

"Stiles! Wait!" Derek exclaimed rushing up after him, and then stopped to glare at the smirking waitress, saying "Don't think that I won't be coming back here tomorrow to complain to your manager!" Now that made her smirk drop.

 

Derek rushed outside, and found Stiles leaning against the Camaro, trying to open the passenger door, but failing due to it being locked.

"Sti...?" Derek said, tentatively approaching his boyfriend.

 

"Just...just take me home Derek." Stiles said, sounding defeated.

Derek's heart dropped, and be stammered out "But why?"

"Are you serious?" Stiles said with a small self-deprecating laugh.

"Yes i'm serious. It's because of that waitress right?"

"It's not just the waitress Derek! Okay? It's going to be everyone else, if we keep doing this?!"

"What do you mean?!" Derek asked pleadingly.

"I mean...that if you stay with me you're probably just going to be constantly asked why the hell you're with me when you could get anyone, and eventually you're going to see that and then leave me and I can't do that Derek."

"You're an idiot Stiles!" Derek exclaimed, panicking at Stiles's tentative nod and the small tear that dripped down his face. Derek approached him, gently lifting his chin up, and wiped away the tears.

"No hey, Stiles, baby come on. I mean you're an idiot for thinking that! Do you not remember my giant embarrassing confession to you?! I like you Stiles! I like you a lot, and have for forever, and now that I have you...i'm not giving you up. It doesn't matter what shitty waitress or anyone else says, their horribly wrong opinions about you aren't going to change the way I feel okay? I'm in this for the long haul Sti."

"You mean it?" Stiles asked

"Of course I mean it Sti, and I always will."

Derek took Stiles small smile and smashing their lips together to mean he finally understood.

"Now, how about we go spend the rest of this date at yours, maybe some ice cream and Netflix? Your dad's on a night shift right?"

"Yeah, yeah that's sounds good." Stiles said, kissing Derek chastely and getting into the car.

* * *

 

When the pair reached the Stilinskis, they headed into the kitchen, grabbing a pint of their favorite ice cream, Ben & Jerry's Chocolate Fudge Brownie, and two spoons, and then headed up to Stiles's room.

Stiles set up a show on Netflix on his laptop, while Derek kicked off his shoes and layed his letterman jacket over the back of Stiles desk chair, hoping the amber eyed boy would take the hint and wear it once in a while.

 

Derek joined Stiles on the bed, cuddling up to him, and the pair dug into the ice cream while Hugh Laurie told his crew of doctors what they were doing wrong that episode.

 

Ice cream gone, and House still playing, Derek looked over at Stiles, surprised to see the boy already looking at him.

Shutting his laptop and placing it on the ground, Stiles leaned into Derek, and met him in a soft kiss.

The kiss, however, soon turned dirty, and Derek crawled on top of Stiles, straddling his hips.

 

The pair moaned once they started grinding down on each other, the hard lengths of their dicks meeting through their pants. 

Their grinding picked up, and Derek helped Stiles out of his shirt, laughing at Stiles frantic attempt to free Derek of his.

 

Shirtless, the pair ground together a little more, until Derek reached for the button of Stiles's pants, softly asking "Is this okay?"

At Stiles's nod, Derek unbuttoned the pants, sliding them down and off Stiles's legs, licking his lips at the outlines of Stiles's hard cock through his boxer briefs.

Derek met Stiles for a kiss, and helped to take his own pants off.

 

Underwear clad, the pair ground together more, moaning at the sensation of their hard cocks rubbing together through their underwear.

 

"So, what do you want to do?" Derek asked, running a hand down Stiles's chest, grazing a nipple.

"I kinda wanna...blow you? If that's okay?"

Derek moaned lightly at the thought of Stiles's pretty mouth around his cock, and laid on his back saying "Oh yeah that's okay, more than okay actually"

 

Stiles crawled over Derek, straddling him, and kissed him sloppily, before trailing a line of kisses down Derek's torso, stopping to give attention to Derek's nipples reveling in the sounds he pulls from him.

 

Reaching his underwear, Stiles eyes the large bulge that is the outline of Derek's dick in his underwear.

Deciding to just go for it, Stiles takes off Derek's boxer briefs, and...promptly loses any bit of confidence in this that he had, because holy shit is Derek huge, and Stiles has never done this before.

Derek must sense his nervousness, because he leans up, running a hand through Stiles's hair, saying "It's okay if you're not comfortable with this Sti, we can do whatever you're comfortable with, and if it turns out that's nothing right now, then that's fine okay? I'm just as fine cuddling with you as I am anything else."

Stiles is touched by Derek's words, but is still worried. Derek's had this done to him by multiple people, all with experienced, and he doesn't want Derek to be disappointed.

Stiles's filter must have decided to not work and have him say all that out loud, because he suddenly has Derek sitting up, cradling his face, saying "Sti, yeah I've been with other people, and yeah they all were experienced, but none of them were you. I don't care if you're god-awful at this or porn-star good, it'll be good no matter what because it's coming from you. You could probably slobber all over my dick and i'd still get off because it's you." Derek said, trying to use humor to dissipate Stiles's worries. Juding by his small smile Derek succeeded.

 

"Okay, yeah, okay."

"So do you still want to do this?" Derek asked.

"Yeah, yeah I really do."

"Okay" Derek said, lying back.

 

Feeling confident from Derek's words, Stiles decides to go for it, and licks and long stripe up Derek's cock from base to tip.

He tentatively swirls his tongue around the head, taking in the slightly bitter, salty taste of precum, and egged on by Derek's moans, decides to try taking Derek fully into his mouth.

 

Stiles gets about halfway on Derek's dick before he has to pull back, gag reflex making an appearance.

Feeling Stiles gag, Derek runs his hands through Stiles's hair gently, softly saying "Shh, slowly, it's okay Sti, you don't have to try and deep throat right away."

Stiles nods, and gives a small smile, going back in.

 

Bobbing his head, Stiles covers the rest of Derek's length that he can't fit into his mouth with his hand, and starts sucking.

Alternating between short sucks, to hard long ones, and pulling off to lick around the head, it's a matter of time before Derek is frantically saying "Sti, Sti, you need to pull off or i'm going to cum in your mouth."

Moaning at the thought, Stiles redoubles his efforts, until hot, salty liquid is filling his mouth. Trying to get it all, his gag reflex protests and he has to pull off, cum dripping down his lips.

 

After catching his breath, Derek hauls Stiles up, wiping away the cum on his mouth, and kisses him, taking in the slight taste of himself still present in his boyfriend's mouth.

Reaching down to return the favor and jerk his boyfriend off, Derek is met with suprise when his hand touches a slowly softening dick and comes away covered in cum.

Pulling back from the kiss, Derek tries to meet Stiles's gaze, but he refuses, looking to the side.

 

Cradling his chin, Derek turns Stiles towards him until he can meet his gaze, and his heart hurts at the expression of shame and embarrassment marring his boyfriend's beautiful face.

"Sti...?"

"I...i'm sorry Der, I didn't expect that, I-I ruined it i'm sorry." Stiles stammered curling into himself and trying to climb off Derek.

 

Derek held him resolutely in place.

"Sti, you didn't ruin anything and there's nothing to be ashamed of. Yeah, me being able to get you off for the first time would've been fun, but the fact that you came untouched just from getting me off is the hottest thing i've ever experienced."

At the look of doubt on his boyfriend's face, Derek said "No seriously Sti, no one's ever done that before, and that's so hot. The fact that you getting me off made you so hot that you came untouched...wow I can't, that's-that's going to be masterbatory material for weeks, maybe even months."

"Yeah?" Stiles softly asked, looking at Derek from under his lashes.

"Definitely" Derek said, leaning in for a kiss.

Stiles met him for the kiss, returning the gentleness, and then cuddled up on the side of Derek, head over his steadily beating heart.

Derek kissed Stiles forehead, and was slowly lulled to sleep by Stiles's breathing

* * *

 

Two and a Half Months Later

 

Derek and Stiles have been dating for almost three months now and couldn't be happier.

They've met each other's parents and even their friends, and are pleased to note that their friend group meshed so nicely it's like they were never separate groups to begin with.

 

There was some animosity on Stiles's friend's end at first, but once they saw that Derek wasn't actually some bully jock and actually really cared about Stiles they relented.

Now, the pair swear their friend groups hang out more with each other than with them now.

 

Everything is great, except now, the summer is coming to a close, and senior year of school starts tomorrow. And Stiles, well Stiles is worried.

Rationally, he knows Derek cares about him a great deal, even "L word" levels of cares about him, (even though neither have admitted so yet) but Stiles is worried that once school starts, people's opinions are going to make Derek's own opinions change.

But, as of now, Stiles is going to just enjoy Derek for as long as he's able to.

 

 

Derek knows something is up with Stiles. Whenever someone even mentions the words "senior year" he tenses up, and Derek doesn't know why, but since school starts tomorrow, Derek guesses he'll find out soon.

 

Derek pulls up to the Stilinski house and honks the horn, smiling at Stiles flailing his way out of the door.

Pulling open the passenger door and climbing inside, Stiles leans over, kissing Derek on the cheek with a mumbled "morning".

"Mm morning"

 

Driving to the school, Derek looks over at Stiles, taking in his outfit, specifically:

"Oh hey where's my jacket?"

"What jacket?"

"Stiles"

"Oh right! The letterman jacket! Uh, it's in my room."

"Oh uh, I thought you were going to wear it?

"Oh! I was, it's just...my dad was rushing me and I was running late, I must've forgot to grab it." Stiles lies.

"Oh, okay, well there's always tomorrow I guess." Derek says, offering Stiles a small smile.

Stiles returns the smile slightly, saying "Yeah! Always tomorrow!"

Stiles notices Derek's expression start to turn confused, and in an effort to distract him starts to dramatically burst out singing the song "Tomorrow" from Annie.

Stiles smirks when it has the desired effect and makes Derek laugh at his antics, calling him an idiot fondly, and then, they're at the school.

 

Stiles gulps. He really didn't want Derek to drive him to school. But since he's always had the best luck his Jeep shit the bed three days ago and Derek offered to drive him like the good boyfriend he is, and Stiles couldn't think up an excuse fast enough.

So, now here he is, watching as the entirety of Beacon Hill's High watches as he gets out of resident jock Derek Hale's black Camaro.

 

Stiles is snapped from his reverie by Derek shouting "Sti?! Are you just going to stand there all day? You'll be late to homeroom if you don't start moving."

Shrugging his backpack higher, Stiles mumbles a "yeah" trying to ignore the franctic whispering he can already hear walking into the school.

Said whispering turns into an outright roar once Derek grabs his hand, leads him to his homeroom, and kisses him soundly on the mouth, saying see you later, Sti." And walks away.

Today should be fun.

 

 

Derek is seriously worried. The whole day it's seemed like Stiles has been trying to avoid him, or even worse, when around him, pulls away from him. 

Hell, at lunch today Stiles sat on the other side of the table from Derek and three seats down!

Derek feels like he's gotten punched, metaphorically in the heart and physically in the face and he needs to get to the bottom of this before he goes crazy.

Luckily, the last bell just rang, and now as he waits at the Camaro for Stiles, he hopes the confusion will be made clear soon.

 

Derek is definitely worried now. After a silent and frankly awkward car ride to Derek's house, he knows something is wrong with Stiles and is afraid of what it'll be.

 

The pair heads up the stairs to Derek's room, and Derek watches as Stiles tentatively sits down on his bed like he's never been there before, like they didn't just 69 there two days ago. God.

 

"Stiles, we need to talk" Derek says, sitting down, and is struck with worry when he sees Stiles's expression break, lip wobbling, and eyes spilling over with tears.

 

"Sti, Stiles? What's wrong baby?"

"You're-you're breaking up with me!" Stiles sadly exclaims.

"Woah what? Baby! No i'm not?! I'm worried that you're about to break up with me!" Derek exclaims, trying to wipe Stiles's tears away.

"Wha-what?! Why would you think that?!"

"Because you've been pulling away from me all day! You didn't even sit near me at lunch, you've barely let me touch you!"

"Well, yeah, cos I don't want to draw attention."

"Why not? Do you not want people to know we're dating?" Derek asks, sounding hurt.

"No, No Der of course I do! It's just, i'm worried about what they'll think and say and say to you."

"Oh god, Sti this again? Like with the diner on our first date? I told you i'm in this for the long run! No one else's opinions matter! Plus I haven't gotten anything but positive feedback today. The only negative feedback was from Jaime because he's still bitter that I dumped his ass after I found him cheating on me...everyone else has been happy for me. Surprised, but happy. Have you gotten bad feedback or something?"

"No, it's all beed good actually."

"Then, baby, why the freakout?" 

"I don't know...I guess I was overthinking things."

"I guess so" Derek said smiling.

"Sti...I...I love you? Okay? I really really love you. Please don't doubt this, and if something is bothering you please tell me, I was really worried there."

"You love me?! I love you too Der! So, so much, and i'm really sorry I worried you and doubted you."

Smiling at Stiles returning the sentiment, Derek leans in and chastely kisses his boyfriend. "Good" he says against his lips.

 

After kissing for little while, and with Stiles somehow ending up straddling Derek, Stiles pulls back, and says "You know, we accomplished a first today...first I love yous"

"Mm we did" Derek says, tracing down Stiles's plush bottom lip.

"You know, we could...accomplish another first today?" 

Mulling over Stiles's words, it takes Derek a second or so to truly understand their meaning.

For, Derek and Stiles have certainly had lots of sex over the past few months, but they've never gone all the way. For, when they broached the topic, Stiles, amid some stumbling, a little shame, and some embarrassment, admitted that he wasn't ready for the whole penetration thing on either ends, and wanted to wait a while. And Derek, feeling the way he did and does about Stiles, of course was happy to accept his request.

So now, happily shocked is the short way to summarize how Derek is feeling currently.

 

"Stiles...are you sure?"

"Yes Derek, i'm one hundred percent sure, have been for a while, but have been to wrapped up in all these worries to pay attention to it."

"Okay, okay, yeah, so...now?"

"Yes, Der, now, but only if you want to."

"Of course I want to, just uh you're dad isn't going to be home any time soon right? Cos for the first time I want to be able to...take my time" Derek says, slowly caressing Stiles's side.

"He's working a 12 hour shift, won't be home until 2 AM tomorrow."

"Oh thank fuck" Derek says and then promptly surges up and meets Stiles for a dirty kiss.

 

Kisses turning heated, the pair help each other strip until both are naked, slowly grinding on each other, hard cocks rubbing up onto each other.

After a few minutes of this, Stiles says breathlessly "Not that I don't love this Der, but I thought we had other things in mind."

"Mm, right yeah, uh, turn over?"

Following Derek's words, Stiles scrambles off of him and turns over onto his front.

 

Derek reaches into his sidetable drawer where the lube is, and takes it out, along wih a condom.

Derek slowly kisses down Stiles's back, and when he reaches the beginning of his crack, stops, and asks "I want to try something, if that's okay?"

"Mm yeah sure Der anything" Stiles practically moans.

 

Getting the go ahead from Stiles, Derek slowly spreads his cheeks, looking at his hole.

Now, Derek's never thought an asshole could be a pretty area of the body, but he may have to rethink things because Stiles's, well his is just that: pretty.

Dusty pink and furled, its like it's just begging Derek to get his mouth on it, so, that's exactly what he does.

 

At the first touch of his tongue, Stiles moans like he's dying, and Derek can't help but preen. Then, he goes to town.

Alternating between soft, sweet licks, to hard dirty ones, and occasionally jabbing penetrating ones with the tip of his tongue, Derek basks in Stiles's moans, and isn't planning on stopping any time soon, until Stiles says his first coherent words in a while: "Der, Der," Stiles pants, "This is great, but I'm also sure we shouldn't play the Overstimulate the Virgin game tonight, because I could definitely cum from this and i'd rather cum on your cock."

 

Laughing slightly, Derek says a quiet "Okay, okay" and lubes up his fingers.

 

Tracing around Stiles hole with his lube covered finger, Derek takes some comfort in the fact that Stiles told him he's fingered himself when jerking off before, so at least this isn't completely foreign to him. 

Inserting the first finger, Derek moves it gently around, taking in Stiles moans, until after a while he says "Another"

 

Later, three fingers deep, Derek searches for Stiles's prostate, and knows he's successfully found it when Stiles lets out an explosive moan.

Derek plays with the sweet spot relentlessly, while continuing to finger the amber eyed boy, until eventually Stiles cries out "Okay Der i'm ready! Please! If you don't soon i'm going to cum."

"Okay, okay, shh, Sti, i've got you" Derek says, rolling the condom on and lubing up his cock.

 

Once the condom's on and he's lubed, Derek places the head of his cock on Stiles's hole, and kisses his neck, asking "Ready?"

"Yeah" Stiles says, and Derek pushes in.

 

Head in, Derek lets Stiles adjust, whispering soothing words and laying soft kisses on any skin he can find.

When Stiles softly says "okay" Derek starts to push in more, and stops when Stiles says so.

Eventually, after starting and stopping multiple times, Derek is finally fully seated in Stiles, and the pair moan practically in unison at the sensation.

 

Stiles moans out a "move", and Derek complies, gently thrusting back and forth, letting Stiles adjust.

Eventually, Derek hits Stiles's prostate, and it's like everything clicks.

The thrusts start to pick up, and Derek keeps whispering a steady stream of sweet nothings into Stiles's ear, "so beautiful" "so perfect" "can't believe I get to have you" "can't believe you're mine" "feel so good" "so good for me" "Sti" "Sti" Sti", all interspersed with moans from the both of them, until eventually, Derek feels himself getting close.

 

"Ohh, i'm close Sti, are you?"

"Mm, so close Der, fuck" Stiles moans.

"Yeah? Want me to touch you or do you want to try and come untouched?"

"Touch me Der, please touch me" Stiles pants, and so Derek does.

After that, its a little under half a dozen thrusts and strokes later that Stiles falls apart, followed almost immediately by Derek.

 

Panting, Derek pulls out of Stiles, running a hand down his back at his whine of discomfort, and then heads to the bathroom for a washcloth, to help clean the lube off of Stiles.

 

However, when Derek comes back, his heart drops at the hurt look on Stiles's face.

"Sti? Baby? What's wrong?"

Stiles's face snaps up to his, and he says quietly, "I thought...you left"

"You thought I left...naked?"

"Well I couldn't exactly see if you grabed clothes! All I know is i turned over onto my back and you weren't there!"

"Hey, hey, shh Stiles baby, I just went to grab a washcloth for you, I should've said something, i'm sorry."

"Oh, well, okay" Stiles replied lamely.

"You're always jumping to some crazy conclusions huh?" Derek said, partly fondly, as he had Stiles roll back over and gently wiped him down, looking for any sign of any kind of injury, relieved to see none.

"I just...get insecure I guess" Stiles said softly turning onto back onto his back.

Laying down next to him, Derek cuddled up to Stiles, smiling when he laid his head on his heart, reminding him of the time back in the hospital when Stiles first laid on him like this.

"Well you shouldn't, wasn't one of the reasons we did this to accomplish another first...did you forget what our other first was?"

"Yeah, yeah you love me, I get it. I love you tok Der, i'm trying to work on it."

"Well good thing i'm planning on sticking around for a good, solid lifetime, so I can help you."

Smiling, Stiles looked up at Derek, and leaned in for a series of soft, gentle, kisses.

"I never thought i'd be so happy to haven my nose broken" 

"And I never thought i'd be so happy to have broken another person's nose"

Laughing, Stiles lays his head on Derek's chest, listening to his heartbeat, and sighs out an "I love you Der"

Smiling, Derek kisses Stiles's forehead and says "I love you too Sti"

* * *

 

And if, for their first anniversary, and all the ones following, Stiles's and Derek always give each other a nose-themed present, then no one else understands it but them.

 

That is, until Talia takes it upon herself to tell their story in front of all their friends and family at their wedding six years later.

 

And, they may be a little sad that they can no longer laugh at their friend's confusion, but they still have one more secret to themselves...for on the inside of their wedding bands, is a tiny, engraved, nose.

 

 

**Author's Note:**

> Oh man, i'm just gonna...hide. So this was my attempt at smut. Uh, i'm not someone who possesses male organs, but I do read plenty of smut and watch some porn...uh yay? Hope the smut was okay because up until now I either didn't do it at all or didn't detail it. I also may have a thing where I love fics that Derek calls Stiles "Sti" in, if you didn't notice. As always, me and my gratuitous use of ellipses salute you for reading, and hope you enjoyed (:  
> x Kait


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